2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-9-deoxy-PGD2 compounds

ABSTRACT

This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

The present application is a divisional application of Ser. No. 647,363,filed Jan. 8, 1976, now issued as U.S. Pat. No. 4,028,419.

The present invention relates to prostaglandin analogs for which theessential material constituting s disclosure therefor is incorporated byreference here from U.S. Pat. No. 4,028,419.

I claim:
 1. A prostaglandin analog of the formula ##STR1## wherein Y istrans--CH=CH--; wherein M₁ is ##STR2## wherein R₅ is hydrogen or methyl;WHEREIN L₁ is ##STR3## or a mixture of ##STR4## and ##STR5## wherein R₃and R₄ are hydrogen, methyl, or fluoro, the same or different, with theproviso that one of R₃ and R₄ is methyl only when the other is hydrogenor methyl;Wherein g is one, 2, or 3; and Wherein m is one to 5,inclusive.
 2. A compound according to claim 1, wherein m is one or
 2. 3.A compound according to claim 1, wherein m is 4 or
 5. 4. A compoundaccording to claim 1, wherein m is
 3. 5. A compound according to claim4, wherein g is one.
 6. A compound according to claim 5, wherein atleast one of R₃ and R₄ is fluoro.
 7. A compound according to claim 6,wherein R₃ and R₄ are both fluoro.
 8. A compound according to claim 7,wherein R₅ is hydrogen. 9.2-Decarboxy-2-hydroxymethyl-16,16-difluoro-cis-4,5-didehydro-9-deoxy-PGD₁,a compound according to claim
 8. 10.2-Decarboxy-2-hydroxymethyl-16,16-difluoro-15-epi-cis-4,5-didehydro-9-deoxy-PGD₁,a compound according to claim
 8. 11. A compound according to claim 5,wherein at least one of R₃ and R₄ is methyl.
 12. A compound according toclaim 4, wherein R₃ and R₄ are both methyl.
 13. A compound according toclaim 12, wherein R₅ is hydrogen. 14.2-Decarboxy-2-hydroxymethyl-16,16-dimethyl-cis-4,5-didehydro-9-deoxy-PGD₁,a compound according to claim
 13. 15.2-Decarboxy-2-hydroxymethyl-16,16-dimethyl-15-epi-cis-4,5-didehydro-9-deoxy-PGD₁,a compound according to claim
 13. 16. A compound according to claim 5,wherein R₃ and R₄ are both hydrogen.
 17. A compound according to claim26, wherein R₅ is methyl. 18.2-Decarboxy-2-hydroxymethyl-15-methyl-cis-4,5-didehydro-9-deoxy-PGD₁, acompound according to claim
 17. 19.2-Decarboxy-2-hydroxymethyl-15-epi-15-methyl-cis-4,5-didehydro-9-deoxy-PGD₁,a compound according to claim
 17. 20. A compound according to claim 16,wherein R₅ is hydrogen. 21.2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-9-deoxy-PGD₁, a compoundaccording to claim
 20. 22.2-Decarboxy-2-hydroxymethyl-15-epi-cis-4,5-didehydro-9-deoxy-PGD₁, acompound according to claim 20.